Valentine’s Day doesn’t mean you have to head out for a fancy dinner, for some, it is the perfect occasion to dive into the heartwarming and humorous world of romantic comedies. Whether you’re celebrating with a significant other, or friends, or indulging in some self-love, these 50 romantic comedies offer a delightful mix of love, laughter, and those feel-good moments.
Also, don’t forget to view our collection of Friday night movies where we recommend a new movie each week.
50 Rom Coms To Watch On Valentine’s Day
From timeless classics to modern tales, here’s your ultimate Rom Com Valentine’s Day movie watchlist.
When Harry Met Sally… (1989)
Can men and women ever just be friends? This film navigates the complexities of friendship and love over the years.
Cast: Billy Crystal, Meg Ryan, Carrie Fisher
10 Things I Hate About You (1999)
A modern retelling of Shakespeare’s “The Taming of the Shrew,” set in a high school, where a dating scheme leads to unexpected romance.
Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
The Princess Bride (1987)
A fairy tale adventure about a beautiful young woman and her one true love. They must battle the evils of the mythical kingdom of Florin to be reunited.
Cast: Cary Elwes, Robin Wright, Mandy Patinkin
Pretty Woman (1990)
A wealthy businessman hires an escort for social events, but their relationship becomes more than transactional.
Cast: Richard Gere, Julia Roberts, Jason Alexander
Clueless (1995)
A rich high school student tries to boost a new pupil’s popularity, but reckons with her own existential crisis.
Cast: Alicia Silverstone, Stacey Dash, Brittany Murphy
Four Weddings and a Funeral (1994)
A British comedy about a man falling for a woman at different weddings and a funeral.
Cast: Hugh Grant, Andie MacDowell, Kristin Scott Thomas
Bridget Jones’s Diary (2001)
A year in the life of a thirty-something single woman, full of romantic misadventures and a quest for love.
Cast: Renée Zellweger, Colin Firth, Hugh Grant
Crazy Rich Asians (2018)
A woman learns her boyfriend comes from one of the wealthiest families in Singapore.
Cast: Constance Wu, Henry Golding, Michelle Yeoh
Notting Hill (1999)
A British bookseller meets a high-profile American actress. They try to make their unlikely relationship work amidst the media frenzy.
Cast: Hugh Grant, Julia Roberts, Rhys Ifans
Love Actually (2003)
This ensemble film explores the complexities of the one emotion that connects us all: love.
Cast: Hugh Grant, Martine McCutcheon, Liam Neeson
500 Days of Summer (2009)
A greeting-card writer reflects on his 500 days with Summer, exploring the unpredictable nature of love.
Cast: Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend
The Proposal (2009)
A Canadian executive forces her young assistant to marry her to avoid deportation. Unexpected feelings ensue.
Cast: Sandra Bullock, Ryan Reynolds, Mary Steenburgen
Silver Linings Playbook (2012)
After losing everything, Pat Solitano moves back with his parents and tries to reconcile with his ex-wife, finding an unexpected connection with a mysterious woman.
Cast: Bradley Cooper, Jennifer Lawrence, Robert De Niro
Sleepless in Seattle (1993)
A grieving widower’s son calls a radio talk-show to find his father a partner.
Cast: Tom Hanks, Meg Ryan, Ross Malinger
My Big Fat Greek Wedding (2002)
A Greek woman’s family has concerns about her marrying a man who is not Greek.
Cast: Nia Vardalos, John Corbett, Michael Constantine
There’s Something About Mary (1998)
A man gets a chance to meet up with his dream girl from high school.
Cast: Cameron Diaz, Matt Dillon, Ben Stiller
You’ve Got Mail (1998)
Two business rivals despise each other at work but fall in love over the internet.
Cast: Tom Hanks, Meg Ryan, Greg Kinnear
Amélie (2001)
A shy waitress decides to change the lives of those around her for the better.
Cast: Audrey Tautou, Mathieu Kassovitz, Rufus
La La Land (2016)
A musician and an aspiring actress fall in love but face difficulties as they become more successful.
Cast: Ryan Gosling, Emma Stone, John Legend
To All the Boys I’ve Loved Before (2018)
A teenage girl’s secret love letters are exposed and wreak havoc on her love life.
Cast: Lana Condor, Noah Centineo, Janel Parrish
Roman Holiday (1953)
A princess escapes her royal duties for a night to explore Rome on her own and falls in love with an American journalist.
Cast: Audrey Hepburn, Gregory Peck, Eddie Albert
The Big Sick (2017)
Based on a true story, a couple deals with their cultural differences as their relationship grows amidst a medical crisis.
Cast: Kumail Nanjiani, Zoe Kazan, Holly Hunter
About Time (2013)
A young man with the ability to time travel discovers that finding true love isn’t as easy as he thought it would be.
Cast: Domhnall Gleeson, Rachel McAdams, Bill Nighy
Crazy, Stupid, Love. (2011)
A middle-aged man’s life changes dramatically when he finds out his wife is cheating on him and seeks to rediscover his manhood.
Cast: Steve Carell, Ryan Gosling, Julianne Moore
Annie Hall (1977)
The quirky relationship between a neurotic comedian and a quirky singer shows the ups and downs of love through a series of fragmented memories.
Cast: Woody Allen, Diane Keaton, Tony Roberts
Knocked Up (2007)
A one-night stand with unforeseen consequences leads to a comedic journey of love, responsibility, and growing up.
Cast: Seth Rogen, Katherine Heigl, Paul Rudd
The Holiday (2006)
Two women with guy-problems swap homes in each other’s countries, where they each meet a local guy and fall in love.
Cast: Cameron Diaz, Kate Winslet, Jude Law
Eternal Sunshine of the Spotless Mind (2004)
A couple undergoes a procedure to erase memories of their relationship, which leads to them discovering what they had in the first place.
Cast: Jim Carrey, Kate Winslet, Tom Wilkinson
Moonrise Kingdom (2012)
Two young lovers flee their town, prompting a local search party to go out and find them.
Cast: Jared Gilman, Kara Hayward, Bruce Willis
Sixteen Candles (1984)
A young girl’s “sweet” sixteenth birthday becomes anything but special as she suffers from every embarrassment possible.
Cast: Molly Ringwald, Anthony Michael Hall, Justin Henry
What If (2013)
A medical school dropout who has given up on love meets a woman who changes his perspective on life and love.
Cast: Daniel Radcliffe, Zoe Kazan, Adam Driver
Palm Springs (2020)
Stuck in a time loop, two wedding guests develop a budding romance while living the same day over and over again.
Cast: Andy Samberg, Cristin Milioti, J.K. Simmons
The 40-Year-Old Virgin (2005)
A middle-aged man’s friends try to help him lose his virginity while he falls in love for the first time.
Cast: Steve Carell, Catherine Keener, Paul Rudd
Forgetting Sarah Marshall (2008)
After a devastating break-up, a man takes a Hawaiian vacation only to find his ex is staying at the same resort.
Cast: Jason Segel, Kristen Bell, Mila Kunis
50 First Dates (2004)
A veterinarian falls for a woman with short-term memory loss, where every day he tries to win her love again.
Cast: Adam Sandler, Drew Barrymore, Rob Schneider
Groundhog Day (1993)
A weatherman finds himself living the same day over and over again and learns life lessons along the way.
Cast: Bill Murray, Andie MacDowell, Chris Elliott
Say Anything… (1989)
An underachieving high school graduate falls in love with a high-achieving class valedictorian, leading to an iconic romance.
Cast: John Cusack, Ione Skye, John Mahoney
The Wedding Singer (1998)
A wedding singer’s life takes a turn when he is left at the altar, but a new love promises to renew his faith in love.
Cast: Adam Sandler, Drew Barrymore, Christine Taylor
Hitch (2005)
A smooth-talking dating coach finds himself falling for a tabloid reporter who’s out to expose him as a scam artist.
Cast: Will Smith, Eva Mendes, Kevin James
As Good as It Gets (1997)
A cranky, bigoted, obsessive-compulsive writer finds his life turned upside down when he starts to care for his gay neighbour’s dog, leading to an unlikely friendship and an unexpected romance.
Cast: Jack Nicholson, Helen Hunt, Greg Kinnear
Chasing Amy (1997)
A comic book artist falls for a fellow artist, leading to a complex exploration of friendship and love.
Cast: Ben Affleck, Joey Lauren Adams, Jason Lee
The Notebook (2004)
A young couple falls in love during the early 1940s, but their relationship faces challenges from their social differences.
Cast: Ryan Gosling, Rachel McAdams, James Garner
Legally Blonde (2001)
A sorority girl enrols in Harvard Law School to win back her ex-boyfriend and discovers she has a knack for law.
Cast: Reese Witherspoon, Luke Wilson, Selma Blair
Juno (2007)
A quirky teenager faces an unplanned pregnancy and makes an unconventional decision regarding her unborn child.
Cast: Ellen Page, Michael Cera, Jennifer Garner
She’s the Man (2006)
A girl disguises herself as her brother to play soccer but complicates her social life and her love life in the process.
Cast: Amanda Bynes, Channing Tatum, Laura Ramsey
Valley Girl (1983)
A San Fernando Valley girl and a punk rocker from the city defy their parents and friends to stay together.
Cast: Nicolas Cage, Deborah Foreman, Elizabeth Daily
Trainwreck (2015)
A magazine writer with a fear of commitment starts to rethink her outlook on relationships when she meets a charming sports doctor.
Cast: Amy Schumer, Bill Hader, Brie Larson
The Goodbye Girl (1977)
A divorced dancer and her daughter must share their apartment with an off-Broadway actor, leading to unexpected romance.
Cast: Richard Dreyfuss, Marsha Mason, Quinn Cummings
Serendipity (2001)
A couple reunites years after the night they first met, fell in love, and separated, convinced that one day they’d end up together.
Cast: John Cusack, Kate Beckinsale, Jeremy Piven
Valentine’s Day (2010)
In this ensemble romantic comedy, the lives of several couples and singles in Los Angeles intertwine over the course of Valentine’s Day. From first dates to long-time commitments, and everything in between, the characters navigate the complexities of love and relationships. Plus for a bonus, Taylor Swift makes a memorable appearance — what more could you want from a Valentine’s Day movie?
Cast: Julia Roberts, Jamie Foxx, Anne Hathaway, Taylor Swift